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organic chemistry

Organic Chemistry 1st edition David R. Klein - Solutions

Identify the number of Ï€ electrons in each of the following compounds.a.b.c.d.e. N'
There are four isomers with molecular formula C4H9Cl. Only one of these isomers (compound A) has a chirality center. When compound A is treated with sodium ethoxide, three products are formed: compounds B, C, and D. Compounds B and C are diastereomers, with compound B being the less stable
There are five constitutional isomers with molecular formula C4H8. One of the isomers exhibits a particularly strong signal at M–15 in its mass spectrum. Identify this isomer, and explain why the signal at M–15 is so strong.
Consider the following sequence of reactions:a) Explain how you could use IR spectroscopy to differentiate between compounds F and G.b) Explain how you could use IR spectroscopy to differentiate between compounds D and E.c) If you wanted to distinguish between compounds B and F, would it be more
Following are the IR spectrum and mass spectrum of an unknown compound. Propose at least two possible structures for the unknown compound. 100 80 20 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm-1) % Transmittance 100 80 - 60- 40- 20- 10 20 30 40 50 60 70 80 mlz m/z Relative Intensity
Following are the IR spectrum and mass spectrum of an unknown compound. Propose at least two possible structures for the unknown compound. 100- 80- 40- 20- 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm-1) % Transmittance 100 80- 60- 40- 20- 10 20 30 40 50 60 70 80 90 100 mlz Relative
Calculate the HDI for each molecular formula.a) C4H6 b) C5H8 c) C40H78 d) C72H74e) C6H6O2 f) C7H9NO2 g) C8H10N2O h) C5H7Cl3i) C6H5Br j) C6H12O6
The following mass spectrum is for octane.a) Which peak represents the molecular ion?b) Which peak is the base peak?c) Draw the structure of the fragment that produces the base peak. 100 80 60 40 20 110 10 20 30 40 50 60 70 80 90 100 m/z Relative Intensity
Propose a molecular formula that fits the following data.a) A hydrocarbon (CxHy) with a molecular ion peak at m/z = 66b) A compound that absorbs IR radiation at 1720 cm-1 and exhibits a molecular ion peak at m/z = 70
When treated with a strong base, 2-bromo-2,3-dimethylbutane will undergo an elimination reaction to produce two products. The choice of base (ethoxide vs. tert-butoxide) will determine which of the two products predominates. Draw both products and determine how you could distinguish between them
The mass spectrum of 2-bromopentane shows many fragments.a) One fragment appears at M–79. Would you expect a signal at M–77 that is equal in height to the M–79 peak? Explain.b) A fragment appears at M–15. Would you expect a signal at M–13 that is equal in height to the M–15 peak?
The mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. One appears at m/z = 111 and the other appears at m/z = 97. Identify the structure of each of these fragments.
Compare the structures of cyclohexane and 2-methyl- 2-pentene.a) What is the molecular formula of each compound?b) What is the HDI of each compound?c) Can high-resolution mass spectrometry be used to distinguish between these compounds? Explain.d) How would you differentiate between these two
The sex attractant of the codling moth gives an IR spectrum with a broad signal between 3200 and 3600 cm-1 and two signals between 1600 and 1700 cm-1. In the mass spectrum of this compound, the molecular ion peak appears at m/z = 196, and the relative abundance of the molecular ion and the (M+1)
Match each compound with the appropriate spectrum.a.b.c.d. .CI OH Br ZHN
The mass spectrum of an unknown hydrocarbon exhibits an (M+1) peak that is 10% as tall as the molecular ion peak. Identify the number of carbon atoms in the unknown compound.
Propose a molecular formula for a compound that has one degree of unsaturation and a mass spectrum that displays a molecular ion signal at m/z = 86.
Identify the molecular formula for each of the following compounds, and then predict the mass of the expected molecular ion in the mass spectrum of each compound.a.b.c.d.e. Он
Identify the characteristic signals that you would expect in the diagnostic region of an IR spectrum of each of the following compounds.a.b.c.d.e.f. OH
Identify how IR spectroscopy might be used to monitor the progress of each of the following reactions.a.b.c.d.e. H2 Pt но Он [0]
Identify the signals you would expect in the diagnostic region of the IR spectrum for each of the following compounds.a.b.c.d. z:
What structural features are present in a compound with molecular formula C10H20O?
Propose the only possible structure for a compound with molecular formula C4H6 that exhibits a signal at 2200 cm-1 in its IR spectrum.
Propose all possible structures for a compound with molecular formula C4H8O that exhibits a broad signal between 3200 and 3600 cm-1 in its IR spectrum and does not contain any signals between 1600 and 1850 cm-1.
Propose all possible structures for a compound with molecular formula C4H8O that exhibits a signal at 1720 cm-1 in its IR spectrum.
Identify which two compounds shown here have the same degree of unsaturation.C3H8O C3H5ClO2 C3H5NO2 C3H6
Calculate the degree of unsaturation for each of the following molecular formulas.a) C6H10b) C5H10O2 c) C5H9N d) C3H5ClO e) C10H20f) C4H6Br2 g) C6H6 h) C2Cl6 i) C2H4O2 j) C100H200Cl2O16
Draw the transition state for the reaction between ethyl iodide and sodium acetate
Consider the following SN2 reaction:(a) Assign the configuration of the chirality center in the substrate.(b) Assign the configuration of the chirality center in the product.(c) Does this SN2 process proceed with inversion of configuration? Explain. Br CN NaCN DMF
Classify each of the following solvents as protic or aprotic:(a) DMF(b) Ethanol(c) DMSO(d) Water(e) Ammonia
Consider the following reaction:(a) How would the rate be affected if the concentration of the alcohol is doubled?(b) How would the rate be affected if the concentration of HBr is doubled? Br -Он + H20 НЕr
Consider the following reaction:(a) How would the rate be affected if the concentration of the alkyl halide is doubled?(b) How would the rate be affected if the concentration of sodium cyanide is doubled? CN Br NaCN NaBr DMSO
For each of the following pairs of compounds, identify which compound would react more rapidly in an SN2 reaction. Explain your choice in each case.(a)(b)(c)(d) CI .CI Вг Br
Draw all isomers of C4H9I, and then arrange them in order of increasing reactivity toward an SN2 reaction.
List the systematic name and common name for each of the following compounds:(a)(b)(c)(d)(e) CI Br
Melphalan is a chemotherapy drug used in the treatment of multiple myeloma and ovarian cancer. Melphalan is an alkylating agent belonging to the nitrogen mustard family. Draw a likely mechanism for the alkylation process that occurs when a nucleophile reacts with melphalan: NH2 .CI но -N CI
What reagents would you use to accomplish a substitution with retention of configuration; for example? OH SH (R)-2-Butanol (R)-2-Butanethiol
Identify the reagents you would use to accomplish each of the following transformations:(a)(b)(c)(d)(e)(f)(g)(h) OH ОН Br
In Chapter 23, we will learn several methods for making primary amines (RNH2). Each of these methods utilizes a different approach for forming the C€”N bond. One of these methods, called the Gabriel synthesis, forms the C€”N bond by treating potassium phthalimide with an alkyl
Determine whether each of the following reactions proceeds via an SN1 or SN2 mechanism and then draw the product(s) of the reaction:(a)(b)(c)(d)(e)(f) .? Меон, Br cP HMPA
When used as a solvent, will acetone favor an SN2 or an SN1 mechanism? Explain. Acetone
Does each of the following solvents favor an SN2 reaction or an SN1 reaction? a) b) c) d)(e) MeOH (f ) CH3CN (g) HMPA (h) NH3 ОН %24
Consider the structure of the compound below.(a) Identify each position where an SN2 reaction is likely to occur.(b) Identify each position where an SN1 reaction is likely to occur. Cl CI TsO. OMe Br NH2
Identify the number of steps (patterns) for the mechanisms in Problems. For example, the patterns for the first two are:a: ±H± €“ LG €“ Nuc attack This mechanism exhibits a proton transfer before the two core steps.b: ±H± €“ LG €“
Draw the skill the mechanism for each of the following SN1 processes:(a)(b)(c)(d)(e)(f)(g)(h) Br Он HBr Он HBr -Br
For each of the following substrates, determine whether an SN1 process will involve a carbocation rearrangement or not:(a)(b)(c)(d)(e)(f) ОН
Will an SN1 process involving each of the following nucleophiles require a proton transfer at the end of the mechanism?(a) NaSH (b) H2S (c) H2O (d) EtOH (e) NaCN (f) NaCl(g) NaNH2 (h) NH3 (i) NaOMe(j) NaOEt (k) MeOH (l) KBr
For each of the following substrates, determine whether an SN1 process will require a proton transfer at the beginning of the mechanism:(a)(b)(c)(d)(e)(f) -OH
Draw the two products that you expect in the following SN1 reaction and describe their stereoisomeric relationship: Br NaSH
Draw the products that you expect in each of the following SN1 reactions:a.b.c. :? NacI Br Br SH
Identify which of the following substrates will undergo an SN1 reaction more rapidly. Explain your choice. Br Br or
Draw the carbocation intermediate generated by each of the following substrates in an SN1 reaction:a.b.c.d. Br
The following reaction occurs via an SN1 mechanistic pathway:(a) What happens to the rate if the concentration of tert-butyl iodide is doubled and the concentration of sodium chloride is tripled?(b) What happens to the rate if the concentration of tert-butyl iodide remains the same and the
Nicotine is an addictive compound found in tobacco, and choline is a compound involved in neurotransmission. The biosynthesis of each of these compounds involves the transfer of a methyl group from SAM. Draw a mechanism for both of these transformations:a.b. H SAM N' N' Nicotine
Treatment of 5-hexen-1-ol with bromine affords a cyclic product:The mechanism of this reaction involves several steps, one of which is an intramolecular SN2 process:In this step, a bond is in the process of breaking, while another bond is in the process of forming. Draw the transition state of
In Problem 7.4, we saw that an intramolecular substitution reaction can occur when the nucleophilic center and electrophilic center are present in the same compound. Draw the transition state of the reaction in Problem 7.4.When a nucleophile and electrophile are tethered to each other (that is,
Draw the transition state for each of the following SN2 reactions:(a)(b)(c)(d) Br ОН Br Pон
When (S)-1-bromo-1-fluoroethane reacts with sodium methoxide, an SN2 reaction takes place in which the bromine atom is replaced by a methoxy group (OMe). The product of this reaction is (S)-1-fluoro-1-methoxyethane. How can it be that the starting material and the product both have the S
Draw the product for each of the following SN2 reactions:(a) (S)-2-Chloropentane and NaSH (b) (R)-3-Iodohexane and NaCl(c) (R)-2-Bromohexane and sodium hydroxide
The reaction below exhibits a second-order rate equation:(a) What happens to the rate if the concentration of 1-iodopropane is tripled and the concentration of sodium hydroxide remains the same?(b) What happens to the rate if the concentration of 1-iodopropane remains the same and the concentration
For the substitution reaction shown below, assume a stepwise process is taking place and draw the mechanism. + NaCI NaBr Br CI
When a nucleophile and electrophile are tethered to each other (that is, both present in the same compound), an intramolecular substitution reaction can occur, as shown. Assume that this reaction occurs via a concerted process and draw the mechanism. Br BrO
For each of the following reactions assume a stepwise process is taking place and draw the mechanism:(a)(b) Br Br NaCl CI Nal
For each of the following reactions, assume a concerted process is taking place and draw the mechanism:(a)(b) SH Br NaSH NaBr Nal NAOME NaOMe
Assign a systematic name for each of the following compounds:(a)(b)(c)(d) CI Br
Draw the curved arrows that accomplish the following transformation: CI CI H. eон Me Me NEN Me
When an amine is protonated, the resulting ammonium ion is not electrophilic:However, when an imine is protonated, the resulting iminium ion is highly electrophilic:Explain this difference in reactivity between an ammonium ion and an iminium ion. R H CI: Н- 'R An amine An ammonium ion N. CI: R.
Consider the following reaction. Predict whether an increase in temperature will favor reactants or products. Justify your prediction. +
In the presence of a special type of catalyst, hydrogen gas will add across a triple bond to produce a double bond:The process is exothermic. Do you expect a high temperature to favor products or reactants? H2 Catalyst
Identify whether each of the following factors will affect the rate of a reaction:(a) Keq(b) ΔG(c) Temperature(d) ΔH(e) Ea(f ) ΔS
Consider the following reaction:The following rate equation has been experimentally established for this process:Rate = k [HO-] [CH3CH2Br]The energy diagram for this process is shown below:(a) Draw the curved arrows showing a mechanism for this process.(b) Identify the two characteristic
Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.a.b.c.d.e.f.g.
Draw curved arrows for each step of the following mechanism: нӧ: нӧ: Н :Он Н—0: нӧ. но о но: на он но: он Н -O: :он Н- н нӧ: Н нӧ: :он но: H20 н-о
Draw curved arrows for each step of the following mechanism: Н 0;н :бн нон H. нон :бн :б. Н 1-б0
Draw curved arrows for each step of the following mechanism: Н Н. нӧ. :0—н Н н Н TH. Н н об- e :Ӧн нӧ. :ӧн но. он Н-о: Но, ОН Но. H. `H. H.
Draw curved arrows for each step of the following mechanism: N-H N-H N-H Фо- н :ОН Н н н Н ON `H. H. н Н :ОН
Draw curved arrows for each step of the following mechanism: :ö :ö H-OSO3H Н ӧн H I IN- Н ӧн N- NH2 OösoH :ö :ÖSO3H NH2 `NH2 NH2 H-OSO3H Н le н Н CösoH N- -Н-0 Nн, "9 NH2 NH2 H-OSO3H CösoH HEosö: Ө.. -он -ӧн NH2 нн H-OSO3H Cöso,H -н-о Н :5: :Z-I
Draw curved arrows for each step of the following mechanism: но. Он н. НаС -CH;So -сн-S0 Нас NO2
For the following mechanism, identify the sequence of arrow-pushing patterns: Н N:0 Не :он N=N. H N=N. :OH H NEN нн Н
For the following mechanism, identify the sequence of arrow-pushing patterns: н. Н :ÖH :ÖH .R R R H20 Н. jata
For the following mechanism, identify the sequence of arrow-pushing patterns: н :OH :ÖH ÖR H OR H OH :ÖR -Н2о OR ÖR OR
For the following mechanism, identify the sequence of arrow-pushing patterns: :ÖH „ 4-4-1-4 н Ci: RT :RO :RO R.
For the following mechanism, identify the sequence of arrow-pushing patterns: :0: :O: :0: н-ӧ—н H. Н-о-н де RT Он :Cl: H Н
For the following mechanism, identify the sequence of arrow-pushing patterns: н :дн :ӧн :0: н-о-Е ӧМе н-б-Е Н-б—Et Et бе .. OMe O: Et Me Me Et н :Он :0: Н—о—Et -МеOн ӦEL ӦEL ӦEL Me H.
For the following mechanism, identify the sequence of arrow-pushing patterns: Br ОН NO2 esн :ОН Br но Но Вr Но Вr Br Но
For the following mechanism, identify the sequence of arrow-pushing patterns: H. o=0=o: :O: o==o; :O: %ö: o==o: Cö:
For each of the following pairs of compounds, determine the relationship between the two compounds.a.b.c.d.e.f.g.h.i.j.k.l. Me Me -CI CI- Н- -н но н но- -н Me Me
Each of the following compounds possesses a plane of symmetry. Find the plane of symmetry in each compound. In some cases, you will need to rotate a single bond to place the molecule into a conformation where you can more readily see the plane of symmetry.a.b.c.d. но Но
(R)-Limonene is found in many citrus fruits, including oranges and lemons:For each of the following compounds identify whether it is (R)-limonene or its enantiomer, (S)-limonene:a.b.c.d.
When 0.075 g of penicillamine is dissolved in 10.0 mL of pyridine and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is -0.47°. Calculate the specific rotation of penicillamine.
Determine whether each statements is true or false:(a) A racemic mixture of enantiomers is optically inactive.(b) A meso compound will have exactly one non-super-imposable mirror image.(c) Rotating the Fischer projection of a molecule with a single chirality center by 90° will generate the
The specific rotation of (R)-carvone (at 20°C) is -61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had a specific rotation of -55. Calculate the % ee of this mixture.
Predict the geometry for the central atom in each of the compounds below:a) NH3 b) H3O+ c) BH4– d) BCl3 e) BCl4– f) CCl4g) CHCl3 h) CH2Cl2
Rank the indicated bonds in terms of increasing bond length: Н Н. 1 С—СЕС—Н =C Н—с—С. Н Н Н
Draw a Lewis dot structure for each of the following atoms:(a) Carbon (b) Oxygen (c) Fluorine (d) Hydrogen(e) Bromine (f) Sulfur (g) Chlorine (h) Iodine
Draw all constitutional isomers that have molecular formula C4H10O?
Draw two constitutional isomers that have molecular formula C3H7Cl.
For the following mechanism, identify the sequence of arrow-pushing patterns: CI CI CI CI Lci-Al-CI je CI
Rank the three carbocations shown in terms of increasing stability:a.b.
For each of the following reactions identify the arrow-pushing pattern that is being utilized:a.b.c.d. H,

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